Production of amines of high molecular weight



Patented Jan. 4, less i r 2,104,421,

UNITED STATES PATENT OFFICE- Gesellschaft m. b. fl chemnitz, Germany, a 3 corporation of Germany No Drawing. Application March 14, 1935, Se rlal No. 11,073. In Germany March 17, 1934 8 Claims. (Cl. 260-127) V This invention relates to the production of ing the reaction hydrogen halide or an alky amine compounds containing alkyl radicals of halide is liberated and an alkyl-aryl amino fatty high molecular weight and more particularly acid formed. Failure to obtain 100% 'converto processes. of producing amines having an alkyl sion in this reaction is believed probably due to radical of at least 8 carbon atoms from, lat-amino the shifting of an alkyl radical to the carboxylic fatty acids, the acyl radicals of which contain one group, but the acid may be made available and more carbon atom than the alkyl radical obtained. returned o the Process y Simple salloniflciiflon- In its broader aspects, the present invention In producing the alkyl amines from theaminc comprehends decomposing substituted a-amino fatty acids in accordance with the present inven- 10 high molecular weight fatty acids into high' tion the amino fatty acid is preferably first mixed l0 molecular alkvi amines by heatingthe acids under with the particular inert solvent chosen and the conditions which avoid objectionable side remixture heated at atmospheric pressure to a actions and decompositions whereby almost quan-i temperature of from about 130 to 280 0. Comtitative conversions may be obtained. This remencement of the decomposition may be noticed suit can be very satisfactorily accomplished by by the evolution of carbon dioxide and its com- 15 heating the acids in the presence of an inert solpletion by cessation of its evolution. vent or diluent liquid whichremains as a liquid Example at the temperature necessary for the decomposition. When the process is carried out at at- Three hundred and seventy-fiv Parts y W i ht 90 mospheric pressure the solvent or diluent must of a-anilino stearic acid are dissolved in ten times possess quite. a high temperature boiling point, the amount by weight of paraffin 011 during heatsuch for example, as possessed by parafln oil or ing in which the temperature is slowly increased. liquid petrolatum. When a. temperature of approximately 140 C.

When a solvent of this nature is employed, the is reached a considerable ebullition of gas comtemperature at which the decomposition occurs mences. At a temperature of about 200 to 220 C. can be controlled within narrow limits while gas is evolved at a very rapid rate, but decreases avoiding local overheating and undesired and as the temperature is increased. When a temcostly side reactions leading to carbonaceous deperature of about 280 C. is reached no more gas composition products. is liberated. By proceeding in this manner prac- The process is applicable to the direct productically quantitative results are obtained. For 30 tion of substitued amines, i. e., secondary and each molecule of acid decomposed one molecule tertiary amines containing alkyl radicals of high of carbon dioxide is liberated. At the conclusion molecular weight from substituted a-amino fatty of the operation the paraffin solution is light yelacids containing acyl radicals of high molecular low in color but becomes light brown when cool weight. The substituting radicals may be aliand is at all times completely clear. In order to 35 phatic, aromatic, cycloaliphatic, heterocyciic or isolate the heptadecylaniline, the parafiln soluany combination of the same radicals or different tion is diluted with an equal volume of ether and radicals as dimethyl and ethylphenyl, respecintroduced into asoiution of hydrochloric acid tively. during constant stirring. Heptadecylaniiine hy- Considered from a different point of view, the drochloride forms and precipitates out as a white, 40

" invention might be considered a method confine crystalline substance. If the solution beverting high molecular weight fatty acyl radicals comes too thick for proper treatment it may be into alkyl radicals of about the same molecular diluted by the addition of more ether. When the weight while contained in amine compounds. reaction with hydrochloric acid is complete, the

The acyl radicals convertible by the present procmass is permitted to cool after which the liquid 45 ess include, for example, capric, lauric, myristi is drawn off suitably by suction leaving the white palmitic, stearic, arachic and like acids. 3 crystalline hydrochloride which should be further A very satisfactory method of obtaining the awashed with ice cold ether. The aniline base may amine fatty acids treated in accordance with the be recovered by suspending the hydrochloride in present invention is by reacting a-halo fatty acids hot water and adding sodium hydroxide during 50 with amines. For example, alkyl-aryl-amino stirring until the mass becomes alkaline. An oily fatty acids may be easily obtained by reacting upper layer comprising theaniline base forms and halo fatty acids with mono or dialkyl-aryl-amines, after cooling is removed and dissolved in ether. said alkyl radicals preferably being of low molecu- The ether is washed out of the mass by;means of lar weight, for instance, dimethyl aniline. Durwater until neutrality is reached, the mass then 55 being dried and any ether remaining being distilled off. The base thus obtained is in a substantially pure form.

In a similar manner other amino fatty acids such as for example, diethyl amino stearic acid, monomethyl anilino lauric acid and other analogous compounds which may be derived from cycloaliphatic or heterocyclic bases can be converted into corresponding amines.

It should be understood that the present invention is not limited to the specific compounds and conditions herein specified, but that it is limited only by the terms employed in the appended claims.

I claim:

,1. The process of producing amines of high molecular weight which comprises decomposing by the use of heat in the presence of an inert diluent non-volatile at the temperatures employed a substituted a-aminofatty acid containing an acyl radical of more than 8 carbon atoms substantially only into a substituted a-amino alkyl compound in which the alkyl radical'contains one less carbon atom than the acyl radical, and into carbon dioxider 2. The process of producing amines of high molecular weight comprising heating a substituted oz-SJllil'lO fatty acid containing an acyl radical of high molecular weight in the presence of an inert diluent of a sufliciently high boiling point to remain in a liquid state at the temperatures employed, until reaction takes place with evolution of carbon dioxide.

3. The process of producing amines of high molecular weight comprising adding a substituted a-amino fatty acid containing an acyl radical of more than 8 carbon atoms to an inert diluent of a sufliciently high temperature boiling point to remain in liquid state at the temperatures of the reaction and heating the mass until carbon dioxide is given off.

4. The process of producing amines of high molecular weight comprising heating an alphaamino fatty acid compound of the general formula N-R--OH R: wherein R is an aliphatic hydrocarbon of at least 8 carbon atoms, R1 is selected from a hydrogen atom, and R2 as well, from an aliphatic, an aromatic, and a, cycloaliphatic radical, with an inert diluent of a suificiently high temperature boiling point to remain in liquid state at the temperatures of the reaction until such compound decomposes into a compound of the general formula v R1\ N-R-H R: and carbon dioxide.

5. The process of producing amines of high molecular weight comprising heatin'g an a-anilino high molecular weight fatty acid to a temperature at which the same decomposes into an alkyl aniline, the allgvl radical of which contains one less carbon atom than the acyl radical of the fatty acid, and into carbon dioxide in the presence of an inert diluent which remains in the liquid state at the temperatures employed.

6. The process as described in claim 5 wherein the compound treated is a-anilino stearic acid.

7. The process of producing amines of high molecular weight comprising heating a diethyl alpha-amino fatty acid in which the acyl radical contains more than 8 carbon atoms in the presence of parafiin oil to a temperature at which carbon dioxide is given 01f.

8. The process as described in claim 7 wherein the material treated is diethyl alpha-amino ste aric acid.

ADOLF GRUN. 

